Rapid and highly efficient trimethylsilylation of alcohols and phenols

with hexamethyldisilazane (HMDS) catalysed by in situ generated I₂

using Oxone^®/KI or cerium ammonium nitrate (CAN)/KI systems

under mild conditions

ESKANDAR KOLVARI^a,*, ARDESHIR KHAZAEI^b,*, MOHAMMAD ALI ZOLFIGOL^b,*,

NADIYA KOUKABI^b, MARYAM GILANDOUST^b and NEDA BAKHIT^b

^aDepartment of Chemistry, Faculty of Science, Semnan University, Semnan, Iran

^bFaculty of Chemistry, Bu-Ali Sina University, Hamedan, Post Box No. 4135, Iran

e-mail: kolvari@semnan.ac.ir; khazaei_1326@yahoo.com; zolfi@basu.ac.ir

MS received 9 February 2010; revised 31 January 2011; accepted 24 June 2011

Abstract. Structurally diverse alcohols and phenols were trimethylsilylated in clean and efficient reactions

with hexamethyldisilazane (HMDS) in the presence of a catalytic amount of I₂ generated in situ from

Oxone^®/KI or CAN/KI systems. The reactions occur rapidly in good to high yields in wet CH₂Cl₂ at room

temperature.

Graphical Abstract. Structurally diverse alcohols and phenols were trimethylsilylated with

hexamethyldisilazane (HMDS) in the presence of a catalytic amount I₂

generated in situ from oxone^®/KI or CAN/KI systems.

Keywords. Alcohols; phenols; hexamethyldisilazane; Oxone^®/KI; CAN/KI; in situ generated I₂;

trimethylsilylation.